JP2713380B2 - ジクロロこはく酸ジアルキルの改良製造方法 - Google Patents
ジクロロこはく酸ジアルキルの改良製造方法Info
- Publication number
- JP2713380B2 JP2713380B2 JP63241167A JP24116788A JP2713380B2 JP 2713380 B2 JP2713380 B2 JP 2713380B2 JP 63241167 A JP63241167 A JP 63241167A JP 24116788 A JP24116788 A JP 24116788A JP 2713380 B2 JP2713380 B2 JP 2713380B2
- Authority
- JP
- Japan
- Prior art keywords
- dialkyl
- reaction
- improved process
- present
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 26
- XSCRWBSKSVOZOK-UHFFFAOYSA-N 2,3-dichlorobutanedioic acid Chemical class OC(=O)C(Cl)C(Cl)C(O)=O XSCRWBSKSVOZOK-UHFFFAOYSA-N 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- -1 quinoline-2,3-dicarboxylic acid ester Chemical class 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- MDDBCVZNWKPLAD-VOTSOKGWSA-N (E)-4-anilinooxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)ONC1=CC=CC=C1 MDDBCVZNWKPLAD-VOTSOKGWSA-N 0.000 description 2
- QDXJFRHCHWDQSP-UHFFFAOYSA-N 1,4-dihydroimidazol-5-one;quinoline Chemical compound O=C1CNC=N1.N1=CC=CC2=CC=CC=C21 QDXJFRHCHWDQSP-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 2
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YHUVMHKAHWKQBI-UHFFFAOYSA-N quinoline-2,3-dicarboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(C(=O)O)=CC2=C1 YHUVMHKAHWKQBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- XQRVITDMGTWTIC-VURMDHGXSA-N (Z)-2-anilinobut-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)/NC1=CC=CC=C1 XQRVITDMGTWTIC-VURMDHGXSA-N 0.000 description 1
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
- PBHUSRBVKLAGGU-UHFFFAOYSA-N 2-carbamoylquinoline-3-carboxylic acid Chemical class C1=CC=C2C=C(C(O)=O)C(C(=O)N)=NC2=C1 PBHUSRBVKLAGGU-UHFFFAOYSA-N 0.000 description 1
- KLGHXRFGBQXCBN-UHFFFAOYSA-N 3-(4,5-dihydroimidazol-1-yl)quinoline-2-carboxylic acid Chemical class OC(=O)C1=NC2=CC=CC=C2C=C1N1CCN=C1 KLGHXRFGBQXCBN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- PBGMSGHICSEALQ-UHFFFAOYSA-N diethyl 2,3-dichlorobutanedioate Chemical compound CCOC(=O)C(Cl)C(Cl)C(=O)OCC PBGMSGHICSEALQ-UHFFFAOYSA-N 0.000 description 1
- JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 description 1
- STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 1
- 229940071094 diethyl oxalacetate Drugs 0.000 description 1
- NLVZUORLSQCGFQ-UHFFFAOYSA-N furo[3,4-b]quinoline-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=NC2=C1 NLVZUORLSQCGFQ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10145487A | 1987-10-01 | 1987-10-01 | |
| US101454 | 1987-10-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01113346A JPH01113346A (ja) | 1989-05-02 |
| JP2713380B2 true JP2713380B2 (ja) | 1998-02-16 |
Family
ID=22284736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63241167A Expired - Lifetime JP2713380B2 (ja) | 1987-10-01 | 1988-09-28 | ジクロロこはく酸ジアルキルの改良製造方法 |
Country Status (21)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL152339A0 (en) * | 2000-04-21 | 2003-05-29 | Sol Gel Technologies Ltd | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675432A (en) | 1986-08-29 | 1987-06-23 | American Cyanamid Company | Method for the preparation of anilinofumarate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527345A (en) * | 1948-09-18 | 1950-10-24 | Allied Chem & Dye Corp | Preparation of esters of dichlorosuccinic acid |
-
1988
- 1988-08-22 ES ES88113585T patent/ES2042664T3/es not_active Expired - Lifetime
- 1988-08-22 DE DE8888113585T patent/DE3872136T2/de not_active Expired - Lifetime
- 1988-08-22 EP EP88113585A patent/EP0309724B1/en not_active Expired - Lifetime
- 1988-08-22 AT AT88113585T patent/ATE77363T1/de not_active IP Right Cessation
- 1988-08-24 IL IL87558A patent/IL87558A/xx not_active IP Right Cessation
- 1988-09-27 RO RO1988135290A patent/RO101036B1/ro unknown
- 1988-09-28 JP JP63241167A patent/JP2713380B2/ja not_active Expired - Lifetime
- 1988-09-29 DD DD88320262A patent/DD285339A5/de unknown
- 1988-09-29 CA CA000578777A patent/CA1319701C/en not_active Expired - Fee Related
- 1988-09-30 YU YU1838/88A patent/YU45063B/xx unknown
- 1988-09-30 KR KR1019880012833A patent/KR0149635B1/ko not_active Expired - Fee Related
- 1988-09-30 CS CS651188A patent/CS274683B2/cs not_active IP Right Cessation
- 1988-09-30 ZA ZA887374A patent/ZA887374B/xx unknown
- 1988-09-30 BR BR8805059A patent/BR8805059A/pt not_active IP Right Cessation
- 1988-09-30 IE IE296388A patent/IE64553B1/en not_active IP Right Cessation
- 1988-09-30 AU AU23303/88A patent/AU614544B2/en not_active Ceased
- 1988-09-30 HU HU885101A patent/HU203313B/hu not_active IP Right Cessation
- 1988-09-30 RU SU884356610A patent/RU2032659C1/ru not_active IP Right Cessation
- 1988-09-30 AR AR88312092A patent/AR246731A1/es active
- 1988-09-30 BG BG085573A patent/BG47346A3/xx unknown
-
1992
- 1992-06-18 GR GR910402236T patent/GR3004936T3/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675432A (en) | 1986-08-29 | 1987-06-23 | American Cyanamid Company | Method for the preparation of anilinofumarate |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE77363T1 (de) | 1992-07-15 |
| AU2330388A (en) | 1989-04-06 |
| IL87558A0 (en) | 1989-01-31 |
| BG47346A3 (en) | 1990-06-15 |
| HU203313B (en) | 1991-07-29 |
| BR8805059A (pt) | 1989-05-09 |
| RO101036B1 (en) | 1992-11-23 |
| DD285339A5 (de) | 1990-12-12 |
| CS274683B2 (en) | 1991-09-15 |
| EP0309724B1 (en) | 1992-06-17 |
| KR890006561A (ko) | 1989-06-14 |
| KR0149635B1 (ko) | 1998-10-15 |
| ZA887374B (en) | 1989-06-28 |
| DE3872136D1 (de) | 1992-07-23 |
| AR246731A1 (es) | 1994-09-30 |
| YU183888A (en) | 1990-02-28 |
| GR3004936T3 (enrdf_load_stackoverflow) | 1993-04-28 |
| JPH01113346A (ja) | 1989-05-02 |
| DE3872136T2 (de) | 1992-12-03 |
| CA1319701C (en) | 1993-06-29 |
| EP0309724A1 (en) | 1989-04-05 |
| AU614544B2 (en) | 1991-09-05 |
| ES2042664T3 (es) | 1993-12-16 |
| IE64553B1 (en) | 1995-08-23 |
| IE882963L (en) | 1989-04-01 |
| RU2032659C1 (ru) | 1995-04-10 |
| CS651188A2 (en) | 1991-03-12 |
| IL87558A (en) | 1993-03-15 |
| YU45063B (en) | 1991-06-30 |
| HUT47896A (en) | 1989-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20071031 Year of fee payment: 10 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081031 Year of fee payment: 11 |
|
| EXPY | Cancellation because of completion of term |